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Does anybody here regret RE (for not-financial reasons)?
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I'm 56 and currently working full time for someone else and own my own side business. I just reached my financial milestone for retiring early (wahoo!) and am beyond ready to stop sucking up to bosses and their whims. I love my business; been doing it for almost 5 years now and want to dedicate more time to growing it. I also just want to get rid of the stress of bosses who make my work life miserable. But I worry that I might be falling into the "grass is greener" fallacy.

I know there will always be things that annoy me or frustrate me. But I think quitting the full time jobs will get rid of the larger portion of it, and more importantly, get rid of the feeling of helplessness you have when you have to keep a boss happy. I adore the autonomy of my business, even when it gets into trouble, when it's all on me as to whether it succeeds or fails, I rise to that challenge. But having a boss that makes me feel like a stupid idiot and being unable to step him back, or having unreasonable workload, or being required to do counter productive or busywork just because the boss says so? I can't stand that.

I get so frustrated and discouraged at work that my brain shuts down and I just stop working for a while. It's been like this for a whole string of professional jobs for the last 10 years. I don't think getting a new job will be any better.

My husband loves his job (where in contrast to my situation he has a management level job with some autonomy mixed with technical work that he loves) and is paid well enough to support us both. So we could continue to live fairly well on just his salary and not pull down on my retirement savings until I'm of the "correct" age to retire. But if something happened to him (I hope not, he's another joy in my life!), I could then live on my retirement savings.

So, thoughts? Should I retire from the day job and focus on my business? Or am I looking at things through rose-tinted glasses?

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4 years ago